Toluene → N-methylbenzothiazolone

Participants

Reaction Steps

Benzothiazolone (3.78 g, 0.025 mole) was dissolved in a solution of sodium hydroxide (1.60 g, 0.0375 mole) in water (100 c.c.), and tetra-n-butylammonium bromide (0.24 g, 7.5×10-4 mole) and toluene (40 c.c.) were added thereto. Dimethyl sulfate (4.70 g, 0.0375 mole) was added dropwise thereto at room temperature, and the mixture was stirred at room temperature for 1 hour, followed by phase-separation. The toluene layer was washed once with water, and the solvent was removed under reduced pressure to obtain 4.14 g of N-methylbenzothiazolone as white crystals. Yield 100%, purity 97.7%, m.p. 70°-73.5° C.

Provenance & Evidence